The 4 Ballsiest Career Moves by Famous Musicians

4 David Bowie Sets Himself Up for Failure, Alienating a Diverse Audience in 1995 With Some of His Best Work

David Bowie has had a 40-year career in music, the majority of which was spent bucking convention. But that's not why he's in this article. After all, people always talk about the chances Bowie's taken in his career: leaving the success of glam to pursue soul, leaving soul to pursue minimalism and electronica, leaving minimalism and electronica to pursue full-blown pop stardom, and rejecting all that stardom as part of a deliberately pop-unfriendly band, Tin Machine. That's all old news. In fact, you've probably seen cheesy news or Internet segments flashing pics from all of these periods at high speed over Bowie's song "Changes." I was going to embed one of them here, but they're all lame. Here's some great early Bowie instead:

But a career dedicated to individuality and integrity is not what gets you onto this list. If it were, Frank Zappa would have to be here, too. This is a list about seldom-discussed single acts of musical bravery, and for that we have to go to New York in 1995.

Bowie spent the first half of the '90s trying to kill off the pop music fan base he'd acquired in the '80s with Let's Dance and Labyrinth. By 1995, he had done so, and he re-emerged with the incredibly strong and sonically demanding Outside album, produced by his former collaborator Brian Eno. He also teamed up with Trent Reznor and went on tour with Nine Inch Nails at the height of NIN's popularity. Furthermore, the shows were continuous, with the two artists slowly integrating their bands. The show went NIN, NIN plus Bowie, NIN plus Bowie and his band, Bowie and his band plus just Reznor, and then just Bowie and his band for the rest of his show. Got it?

At that precise moment in time, NIN was a much bigger draw than Bowie, but because Trent Reznor is not a disrespectful prick, he rightly allowed Bowie a slightly more exalted position on the bill. Here's the deal, though. The overwhelming majority of the coliseum was there to see NIN. The audience was awash with 14-year-old girls in torn fishnets and black lipstick. Even though they probably went off to college, broadened their musical horizons, and became Bowie fans (considering what a huge NIN influence he is), on that night, they were not. But it gets worse. The Outside album is dense, difficult, and over 70 minutes long. Also, it was released the day before the concert, and Bowie played almost exclusively from it. Accordingly, even the minority of the crowd who was there for Bowie did not know what the hell he was playing. Even I had only heard it all the way through a half-dozen times before the show.

When Trent left the stage, so did half the audience, some of them crying that they didn't get enough Trent. Bowie "ruined the show" for them. (That's an actual quote from some girl I overheard in the parking lot ... moments before I strangled her to death.) So many people left that they let my friends and me fill the empty spot before the stage, and I watched the show literally 10 feet from Bowie. And I felt like the only person in the entire place who enjoyed it.

Let's recap: Bowie plays to one of the largest venues in New York, goes onstage with someone far more popular than he at that specific moment in time, and plays to the other guy's audience. Then he plays only demanding music that his own audience does not know. Bowie played great and tanked. He knew he would. How could he not? And he just didn't care. He did what he wanted to do, able to withstand a stadium's worth of undeserved antipathy and indifference. Some people think it's brave that I read the comments to what I write online. I'm not sure "brave" is a good explanation. I read comments for every reason from narcissism to practicality to masochism, but if there is anything brave about it, it comes from Bowie. More than at any other time in his career, Bowie was my hero that night. Putting himself into the mix in the exact way he wanted, hoping to be appreciated, but not depending upon it. Not having his sense of self shaken. When it was over, he said simply, "Well, you've been very kind to listen to so many songs you don't know. Here's one you do." And then closed with "Under Pressure" with the incomparable Gail Ann Dorsey playing bass and killing Freddie Mercury's parts.

3 Lisa Germano Shows How Badass She Is by NOT Being a Tough Grrl

Hey guys, remember Lisa Germano? No? Oh. Well, she spent the majority of her career playing fiddle in John Mellencamp's band. Here she is hoedowning it up during "Paper in Fire":

In 1993, Germano released her own solo album. That's not surprising. Lots of women started singer-songwriter careers in the '90s. The record companies were signing everyone in support of the then popular Lilith Fair festival. Tori Amos, Sarah McLachlan, Shawn Colvin, Fiona Apple, Paula Cole, and Meredith Brooks were all in the air and all over the radio. And in my super politically correct Northeast liberal arts college, women were reading Naomi Wolf's The Beauty Myth and wondering if giving head would make them a member of an oppressed class.

Paula Cole touted her unshaved pits. Tori Amos and Sarah McLachlan sang about rape and stalkers. Meredith Brooks told us what a bitch she was, and Jill Sobule let everyone know that she kissed a girl and was like totally OK with it. Clearly, the key to success was to release music adhering to the then omnipresent theme of grrl power. And into that mix, Lisa Germano releases "You Make Me Want to Wear Dresses":

A simple, catchy tune about how her love makes her feel all girly and gives her the desire to embrace traditional roles. Releasing this song in 1993 would be the equivalent of some LA-based rap group following NWA's "Fuck Tha Police" with "Thank You for Keeping Our Neighborhood Safe, Officer."

No one cares about the song. It didn't do well or establish a brand new solo career, but it bucked all calculating conventional wisdom in the air at that time. It was the song she wanted to make, and she made it, and I can't think of any definition of being empowered beyond that.

2 Scott Walker Rejects Pop Stardom for the Avant-Garde

Hey, ever heard of the Walker Brothers? Yeah, me either, until my buddy Blind Boy from the Rubber Bandits turned me on to them and, more importantly, their frontman, Scott Walker. Apparently, for a moment in the mid-'60s, they were on the receiving end of accolades reserved for the likes of the Beatles. They were wildly successful and known for their dreamy frontman's distinctive baritone vocals.

Anyway, instead of being part of a wildly successful pop group, Scott Walker decided to make incredibly obscure avant-garde soundscapes, a transformation so unexpected and extreme, one critic described it as "Andy Williams reinventing himself as Stockhausen." To put that in perspective for younger readers: going from being Justin Bieber to ... I don't know, someone complex and important you've never heard of because you don't listen to stuff like that because I just had to patronize you with a Justin Bieber reference.

Walker's music is obtuse, dramatic, and extreme, and I could link clips like this, but on one listen it wouldn't make much of an impression. And if it did, it probably wouldn't be a very good one. At the end of the day, perhaps the best proof of what an important musician Walker is would be this audio clip from 1995 in which he calls in to a radio show to wish David Bowie a happy birthday. Even from the mere audio, you can hear David Bowie -- already regarded as his generation's pre-eminent musical provocateur -- utterly lose his shit and his mind that Scott Walker is even talking to him:

1 John Lennon Has the Guts to Do What He'd Slammed Paul McCartney for Doing

It's slowly changing, but John Lennon gets a lot of praise for the Beatles, and Paul McCartney seems to take a lot of shit. History remembers Lennon as the more earnest poet, writing music like "Strawberry Fields Forever," and McCartney as the more fluffy songsmith of things like "Yellow Submarine." For the most part, those classifications are crap, and true Beatles fans don't think in those terms. McCartney wrote some of the Beatles' raunchiest songs, like "Helter Skelter" and "Why Don't We Do It in the Road?" while Lennon certainly wrote his share of fluff, like "Good Night." Both men enjoyed rock and blues and pure pop. And some of Lennon's greatest compositions benefited greatly from McCartney (check out McCartney's bass and drums on "Dear Prudence." Yeah, he plays the drums on that.)

Lots of factors have led to this characterization: Paul was more conventionally cute and boyish-looking, Paul had a smoother, higher tenor voice, and Paul lived longer and produced a lot more incredibly mediocre solo material. But some of the biggest blame for the McCartney slander belongs to John Lennon himself, who said some very not nice things about Paul in the press and got George Harrison to play on the acerbic and vicious "How Do You Sleep?" which paints Paul as a sellout.

Paul's response was to write a massive No. 1 hit called "Silly Love Songs," in which he sings:

"Some people want to fill the world with silly love songs
And what's wrong with that?
I'd like to know, because here I go again
I love you"

Yep, a massive hit with a chorus that's was merely "I love you." The most brilliantly passive-aggressive fuck you ever.

And it's pretty hard to beat up on McCartney for writing love songs when he spent the '70s in a blissful marriage to Linda McCartney, whereas Lennon's decade was more tumultuous, with a rocky relationship with Yoko and some heroin problems. But by 1980, Lennon's life had sorted out. He was back together with Yoko, spending time with his baby, Sean, and getting back to recording. In short, his life was more closely resembling that of McCartney, who had already thrown himself into a stable family life. The result is Lennon's great work on his final album, Double Fantasy. Now, don't get me wrong: I love the album, but basically it's a bunch of silly love songs. Take a listen to "(Just Like) Starting Over" or "Woman."

Basically, after spending the '70s perfecting an image as the true troubled artist, responsible for the most "legit" Beatles and solo music, John Lennon seemed to remember that, much like his friend Paul McCartney, he liked pop music and love songs. Double Fantasy would be deemed saccharine if it weren't so sincere and catchy. Still, it took tremendous balls to release such a simply romantic album after spending 10 years talking politics and publicly dumping on his former partner for writing pop songs. Clearly, Lennon was aware of the public's perception. I remember listening to "The Lost Lennon Tapes" as a boy and hearing him mock "Woman" during the recording by comparing it to his earlier Beatles composition "Girl." (YouTube has failed me though ...) But he was brave enough to pursue a simple, honest, romantic album, and due to that sincerity, his change of heart reads more like maturity than hypocrisy.

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